Holiday rentals in Osceola

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Top-rated holiday rentals in Osceola

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Top guest favourite

A spacious master bedroom is shown, featuring a bed positioned near large windows that provide expansive views of the surrounding landscape. Soft carpeting covers the floor, and natural light fills the room. A small area is visible to the left, suggesting additional amenities.

Home in Warsaw

The Overlook

Adventure awaits! Enjoy the best sunsets and night skies from high above the shores of Truman Lake. An unforgettable way to unwind! Perfect for romantic getaways, thrill seekers, and tourists alike. Protected forests surround the neighborhood and the historic "Hallmark town" of Warsaw is minutes away. A modern marina is just down the road. Great opportunities for relaxation and recreation abound with memorable times sure to be had! Ask about our romance/birthday packages and pet friendly stays!

ValueLocationLaundry

4.94 out of 5 average rating, 390 reviews

Guest favourite

A screened-in porch features wooden walls and a rustic wooden ceiling, providing a cozy gathering space. Comfortable seating is arranged around a central table, while a standing heater adds warmth. Potted flowers and decorative cushions contribute to a welcoming environment amidst views of lush greenery.

Treehouse in Stockton

Rustic Elegance Treehouse Cabin Stockton Lake, MO

Rustic Elegance tops this Treehouse cabin just a mile from Stockton Lake Dam and 2.5 miles to Stockton Town Center. Enjoy total privacy in this wooded scene looking out over the neighbors cattle as well deer and turkey. Sitting on Bear Creek which is spring fed and a kayak is available to explore the creek for a small fee. Fire pit and Weber grill help round out your evenings pleasures. Grocery store, gas station, restaurants, and shopping are all within 10 minutes. Outside electric included.

FamilyLocationHeating

4.92 out of 5 average rating, 169 reviews

Top guest favourite

A gravel driveway leads through a lush green field, bordered by grassy areas on either side. In the distance, a farmhouse is visible, surrounded by trees under a partly cloudy sky. The natural landscape conveys a sense of open space and tranquility.

Farm stay in Deepwater

"Private" House -30 acres {Bucksaw Marina-Truman}

Have a peaceful stay in a Farm house ! 7 minutes away from Bucksaw Marina 18 minutes to Long Shoals ! Huge Deck to enjoy !15 minutes from Clinton to get groceries or to dine out. 1 bedroom with 2 king size beds and a bunk room with 2 full size beds and 2 twins on top. Plenty of parking . 1 bathroom with a shower. Laundry room with a washer and dryer. 75 inch tv ! Pets are welcome. Small pond to let kids fish! Trails on property to walk or enjoy wildlife! (No hunting on the property allowed)

ValueFamilyTV

4.96 out of 5 average rating, 75 reviews

Top guest favourite

Home in El Dorado Springs

Country Paradise

Surrounded by farmland, grazing cattle, blue skies & green grass, enjoy this little piece of country paradise. Looking for a clean place to stay while in the area or while you hunt, this is it. DIRECTLY across the road you can enter over 2400 acres of Missouri Conservation Land, known as Linscomb Wildlife Area! Also nearby are the Sac and Osage Rivers, that are great for fishing with the latter being known for snagging Spoonbill/Paddlefish. Located between El Dorado Springs and Osceola.

FamilyValueIndoor spaces

5.0 out of 5 average rating, 41 reviews

Top guest favourite

A single-story home features a neutral exterior with green shutters and a metal roof. A front porch with steps leads to the entrance, surrounded by trees. The landscape is covered in autumn leaves, creating a quiet and natural setting.

Home in Deepwater

Truman Lake Family Getaway

Minutes away from Harry S. Truman Dam & Reservoir & the upper end of the Lake of the Ozarks. The lake is a popular fishing destination for crappie, largemouth bass, hybrid stripers, catfish, as well as some of the Nation's finest snagging for spoonbill paddlefish. The surrounding area (110,000 acres) provides plentiful & diverse opportunities, including hiking, horseback riding, golfing, biking, bird watching, off-road vehicle adventures, & some of the best hunting in the country.

ValueLocationCheckout

4.93 out of 5 average rating, 141 reviews

Top guest favourite

A modern kitchen is visible, featuring stainless steel appliances and ample counter space. A dining area with four wooden chairs is positioned at a central island, while light wood flooring complements the light walls. Decorative plants add a touch of greenery to the space.

Home in Stockton

The Voyager at Lake Town Estates *HOT TUB*

Welcome to Lake Town Estates! Located only minutes away from the beloved lake town of Stockton, MO, this home offers everything you need for your lake vacation or quiet getaway! Nearby, you will find a local grocery store, a small-town coffee shop/cafe, and a variety of things to do, such as kayaking, hiking, boating, and more! Whether you're bringing the whole family or travelling alone, The Voyager at Lake Town Estates will be the perfect home away from home!

LocationValueSleep quality

4.98 out of 5 average rating, 100 reviews

Guest favourite

Cabin in Osceola

Secluded Cottage in the Woods - with hot tub

Escape to a cozy American Cottage tucked away in the woods, bordered by 900 acres of public Corps of Engineers land—perfect for hunters, fishermen, or anyone craving peace and quiet. Less than a mile away, access Weaubleau Creek, which feeds into the Osage River. Sip coffee on the patio, explore the wet-weather creek, or spend the evening relaxing in the hot tub beneath the stars. A secluded place to slow down, reconnect, and do absolutely nothing at all.

ValueLocationHot tub

5.0 out of 5 average rating, 5 reviews

Top guest favourite

The cottage is nestled among dense trees, featuring a welcoming front porch with white railings. Large windows allow natural light to enter, while a set of stairs leads up to the entrance. The surrounding greenery creates a serene, secluded atmosphere.

Cottage in Wheatland

Cozy Woodland Cottage

This cozy cottage in the woods (completed in June 2017) is perfect for a couple seeking a romantic getaway, enjoying a honeymoon, or celebrating an anniversary. (The sofa is a full convertible bed, if others plan to share the 400+ sq. ft. space.) Located in the Lake Hill (formerly Shadow Lake) Golf Course neighborhood (course is currently closed) about a mile from the NW shores of beautiful Pomme de Terre Lake, and about 6 miles south of Lucas Oil Speedway.

FamilyLocationCondition

4.98 out of 5 average rating, 451 reviews

Guest favourite

A modern cabin is positioned on a gravel driveway, surrounded by lush green trees. The exterior features a combination of wood and stone elements, with a covered porch and four sturdy columns enhancing the entrance. Natural light illuminates the windows on both sides.

Cabin in Deepwater

Truman Lake Cabin Super Clean "Private" Getaway!

Quiet serene location! Our personal cabin is located just 400 yards from Truman Lake. Short walk to the cove for wildlife viewing or Higgins' Landing boat launch is just across the highway, and has plenty of parking for vehicle/s, boat trailer, and great bank fishing. Clinton and Warsaw are a 30 min drive, and Iconium is a 12 min drive. Don't forget to look around in the lake feeder creeks, lot's of arrowheads in the area. We now have super fast WI-FI!

LocationFamilyCheck-in

4.91 out of 5 average rating, 169 reviews

Guest favourite

An open living space is showcased, featuring a comfortable sectional sofa, a coffee table, and a dining table surrounded by black chairs. Natural light filters through large windows, enhancing the warm ambiance. A ceiling fan and light fixture add functionality to the inviting area.

Home in Deepwater

Bird Haven

Welcome! The Bird Haven is our family lake house. Surrounded by tranquil nature, you will be at peace with the many beautiful birds that live in the trees. The home is centrally located near several marinas for great fishing and boating. The spacious interior and large patios in the front and back are setup for hosting larger families who need more space. Come stay at our lakehouse and become part of our lake family!

ValueLocationAmenities

4.91 out of 5 average rating, 46 reviews

Top guest favourite

A lakeside pavilion is visible, featuring a metal roof and wooden structure. Benches are placed underneath for seating. Lush green grass surrounds the area, and trees provide shade, with the calm water of the lake reflecting the surrounding greenery.

Home in Wheatland

Lake House - 5 min from the beach

We’re excited to share our family lake house that we are enjoying with our kids , with guests who love nature, relaxation, and quality time with loved ones. It’s family-friendly, with plenty of activities just steps away. There are nearby playgrounds, tennis/baskets courts, soccer/baseball. Bring your boat/Jet Ski or kayaks to enjoy the water. Race track about 10 min away . Boat slips $15/ day 7 min away .

ValueLocationAccess

4.98 out of 5 average rating, 44 reviews

Guest favourite

An open-concept living area features a light wood ceiling and a modern kitchen island with four high stools. A comfortable seating area is visible with a gray sofa and a floor lamp, while soft natural light enters through the window drapes.

Cabin in Wheatland

Hill's Hideaway: Private, River - Front Cabin

Hill's Hideaway is the perfect setting for relaxation. It has the best of both worlds with a quiet setting on the river but close proximity to all the action of the lake. What was originally a childhood family vacation cabin has been fully remodeled with modern, inviting touches that makes it the perfect year-round getaway.

ValueFamilyCleanliness

4.92 out of 5 average rating, 118 reviews